(2S,3S,5R)-2-[3-(1-benzyloxy)]propyl-3-hydroxy-5-(hydroxy)methyltetrahydrofuran

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,5R)-2-[3-(1-benzyloxy)]propyl-3-hydroxy-5-(hydroxy)methyltetrahydrofuran
• 英文别名: (2S,3S,5R)-5-(hydroxymethyl)-2-(3-phenylmethoxypropyl)oxolan-3-ol
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: RFOYQLYCYCHEHC-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-己二烯醇 在 吡啶 、 盐酸 、 AD-mix-α 、 lithium aluminium tetrahydride 、 甲基磺酰胺 、 水 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 、 叔丁醇 为溶剂， 反应 34.5h， 生成 (2S,3S,5R)-2-[3-(1-benzyloxy)]propyl-3-hydroxy-5-(hydroxy)methyltetrahydrofuran
  参考文献：
  名称：

  Direct synthesis of substituted tetrahydrofurans via regioselective dehydrative polyol cyclization cascades

  摘要：

  A one-pot procedure for the conversion of 1,2,4,5-tetraols into substituted tetrahydrofuran moieties has been developed. This involves the regioselective sulfonylation of the terminal hydroxyl of the polyol array followed by sequential oxirane and oxolane formation under basic conditions. A survey of reaction conditions has defined the use of N-(2,4,6-triisopropylbenzenesulfonyl)imidazole as sulfonylation reagent, potassium tert-butoxide as base, and tert-butanol as solvent to be optimal. Under these conditions, 8-O-benzyl-octan-1,2,4,5,8-pentaol was converted stereospecifically into tetrahydrofurans in 62% yield. Polyol substrates were derived from Sharpless asymmetric dihydroxylation of 1,4-dienes. Hence, substituted tetrahydrofurans could be obtained stereospecifically from diene substrates in two operations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00043-1

文献信息

• Direct synthesis of substituted tetrahydrofurans via regioselective dehydrative polyol cyclization cascades
  作者：Amy B Dounay、Gordon J Florence、Akira Saito、Craig J Forsyth

  DOI：10.1016/s0040-4020(02)00043-1

  日期：2002.3

  A one-pot procedure for the conversion of 1,2,4,5-tetraols into substituted tetrahydrofuran moieties has been developed. This involves the regioselective sulfonylation of the terminal hydroxyl of the polyol array followed by sequential oxirane and oxolane formation under basic conditions. A survey of reaction conditions has defined the use of N-(2,4,6-triisopropylbenzenesulfonyl)imidazole as sulfonylation reagent, potassium tert-butoxide as base, and tert-butanol as solvent to be optimal. Under these conditions, 8-O-benzyl-octan-1,2,4,5,8-pentaol was converted stereospecifically into tetrahydrofurans in 62% yield. Polyol substrates were derived from Sharpless asymmetric dihydroxylation of 1,4-dienes. Hence, substituted tetrahydrofurans could be obtained stereospecifically from diene substrates in two operations. (C) 2002 Elsevier Science Ltd. All rights reserved.